2-Hexanone → HCID 49962378, compound

HRID 1909837Notes

Reaction equation

HRID 1909837 reaction equation
Br[C:2]1[S:3][CH:4]=[CH:5][CH:6]=1.[Li]CCCC.[CH3:12][C:13](=[O:18])[CH2:14][CH2:15][CH2:16][CH3:17]>C1COCC1>[S:3]1[CH:4]=[CH:5][CH:6]=[C:2]1[C:13]([OH:18])([CH2:14][CH2:15][CH2:16][CH3:17])[CH3:12]

Participants

5

Reactant 3

HCID 115832-HexanoneHCID 138512-BromothiopheneHCID 178418339Butyllithium

Product 1

HCID 49962378HCID 49962378, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of 2-bromothiophene (24.3 g, 0.15 mol) in dry THF (120 mL) was cooled to −78° C. under nitrogen. A solution of n-BuLi (2.5 M, 66.0 mL, 0.17 mol) was then added slowly, and the resulting mixture was stirred at −78° C. for 2 hours, before 2-hexanone (18.1 g, 0.18 mol) was added slowly. This mixture was stirred at −78° C. for an additional 1 hour, and then allowed to warm to room temperature, and stirred at room temperature overnight. Most of the solvent was removed in vacuo, and the residue was subjected to flash column chromatography on silica gel with a hexane:EtOAc (4:1, slowly up to 3:1, v/v) mixture, leading to a slightly yellow oil as the product (21.4 g, 77.7%).

Workup

  1. additionwas added slowly
  2. temperatureto warm to room temperature
  3. stirringstirred at room temperature overnight
  4. customMost of the solvent was removed in vacuo

Sources & evidence

ORD record
ord-a39f2bc2b4f4467b8c93bd0ad49a19c8
Source dataset
uspto-grants-2013_12
Patent number
US08598575B2

Reaction notes

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